2006
DOI: 10.1021/op060107s
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The Synthetic Versatility of Acyloxyborohydrides

Abstract: Acyloxyborohydrides are unsurpassed in their versatility as reagents in organic synthesis. In addition to their superior ability in effecting reductive amination of aldehydes and ketones, acyloxyborohydrides can reduce nitrogen heterocycles (indoles, quinolines, isoquinolines), imines, enamines, oximes, amides, nitriles, benzylic alcohols, aryl ketones, aldehydes (but not ketones), acetals, -hydroxy ketones, and other substrates. The ability to control chemoselectivity, regioselectivity, and stereoselectivity … Show more

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Cited by 31 publications
(21 citation statements)
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“…In particular, the 1,4-reductive amination products are not observed for various aromatic aldehydes under similar reductive amination conditions with NaBH(OAc) 3 . [4][5][6] In the case of 5-formyl-2 -deoxyuridine 1, the formation of 1,4-conjugated product is probably possible due to the stabilization of dihydrouridine derivative by intramolecular hydrogen bonding. Similar effect of the intramolecular H-bonding was observed for many compounds with analogous enaminone functionality, for example, in the products derived from reactions of 3-formylchromones with amino compounds [16] and for 6-aminomethylene derivatives of 5-oxo-2-phenyl-5,6,7,8-tetrahydroquinazoline.…”
Section: Resultsmentioning
confidence: 99%
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“…In particular, the 1,4-reductive amination products are not observed for various aromatic aldehydes under similar reductive amination conditions with NaBH(OAc) 3 . [4][5][6] In the case of 5-formyl-2 -deoxyuridine 1, the formation of 1,4-conjugated product is probably possible due to the stabilization of dihydrouridine derivative by intramolecular hydrogen bonding. Similar effect of the intramolecular H-bonding was observed for many compounds with analogous enaminone functionality, for example, in the products derived from reactions of 3-formylchromones with amino compounds [16] and for 6-aminomethylene derivatives of 5-oxo-2-phenyl-5,6,7,8-tetrahydroquinazoline.…”
Section: Resultsmentioning
confidence: 99%
“…In all the reported reactions of the reductive amination of f 5 dU, employing various amine components and NaBH 4 or NaBH 3 CN, the secondary amine derivatives of 2 -deoxyuridines were the only isolated amino-modified products. [6][7][8][9][10]14] The scope of f 5 dU reductive amination carried out with NaBH(OAc) 3 was investigated with a series of primary amines of different nucleophilicity (aliphatic and aromatic amines), steric hindrance (t-butylamine) and with additional functionality present (histamine; Table 1). …”
Section: Resultsmentioning
confidence: 99%
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“…In addition to its superior ability in effecting reductive amination of aldehydes and ketones, it can reduce N-heterocycles (indoles, quinolines, and isoquinolines), imines, enamines, oximes, amides, aryl ketones, acetals, and other substrates. 1 STAB-H is a milder and more selective reducing agent than NaBH 4 . The mild nature of STAB-H may be attributed both to the bulky nature of the reagent and to the inductive electron-withdrawing ability of the three acetoxy groups which stabilize the boron-hydrogen bond.…”
Section: Introductionmentioning
confidence: 99%